I completed a 2 year trip in the Caribbean with my now wife, a large Springer Spaniel and a cranky 13 year old cat. We had a great time.
Suggest all who goes try to time their trip to follow the races down.
Barts Bucket Cup and Antigua Race Week. A lot of special events
that you will rarely see on the normal island time.

If I only had 6 days in the Bahamas I doubt I would be able to find the places to clear in. However always on the French islands. They are free.
Trinidad is only $10. Most Islands they are between $20 and $50. The DR is $83. kinda of high but OK. You really don't have much choice because
they actually rowed out at 8:00am and boarded us! Everyone else too!

Regarding maintenance cost I noticed people who was pushing the amps
did replace batteries and alternators. We used ice.

Half of the boaters didn't have insurance as we didn't. It just cost too much. Be careful. I doubt if a boat hit us he would have insurance.......I had good ground tackle. All Chain. Better Insurance!!

We spent $500 a month once we got in the Caribbean. We rushed thru the Bahamas. I liked the water in the Bahamas. So clear good fishing. However everything was expensive. Poor selection of Food and costly. Never got that warm and fuzzy feeling from the natives either. Oh caught the fish on a hand line between islands...